2-bromomethyl-1,3,3-trimethyl-4-(tert-butyldimethylsilyloxy)methylcyclohex-1-ene

Base Information

Chemical Name:2-bromomethyl-1,3,3-trimethyl-4-(tert-butyldimethylsilyloxy)methylcyclohex-1-ene
CAS No.:174788-43-3
Molecular Formula:C₁₇H₃₃BrOSi
Molecular Weight:361.438
Hs Code.:

Synonyms:2-bromomethyl-1,3,3-trimethyl-4-(tert-butyldimethylsilyloxy)methylcyclohex-1-ene

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Chemical Property of 2-bromomethyl-1,3,3-trimethyl-4-(tert-butyldimethylsilyloxy)methylcyclohex-1-ene

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Technology Process of 2-bromomethyl-1,3,3-trimethyl-4-(tert-butyldimethylsilyloxy)methylcyclohex-1-ene

There total 14 articles about 2-bromomethyl-1,3,3-trimethyl-4-(tert-butyldimethylsilyloxy)methylcyclohex-1-ene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 171504-24-8
[5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,6,6-trimethyl-cyclohex-1-enyl]-methanol

: 174788-43-3
2-bromomethyl-1,3,3-trimethyl-4-(tert-butyldimethylsilyloxy)methylcyclohex-1-ene

Guidance literature:: With triphenylphosphine dibromide 1:1 addition complex; triethylamine; In dichloromethane; at -78 ℃; for 1h;
DOI:10.1016/S0040-4039(00)79157-X

Reference yield:

: 117106-83-9
4-(tert-Butyl-dimethyl-silanyloxymethyl)-3-methyl-cyclohex-2-enone

: 174788-43-3
2-bromomethyl-1,3,3-trimethyl-4-(tert-butyldimethylsilyloxy)methylcyclohex-1-ene

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) cuprous iodide, 3.) triethylamine / 1.) toluene, diethyl ether, 0 deg C, 10 min, 2.) toluene, diethyl ether, 0 deg C, 30 min, 3.) toluene, diethyl ether, 0 deg C, 1 h, 21 deg C, 4 h

2: 55 percent / titanium tetrachloride / CH₂Cl₂ / 1 h / 0 °C

3: 95 percent / toluene; diethyl ether / 0.67 h / 0 - 21 °C

4: hydrogen fluoride / acetonitrile / 0.25 h / Heating

5: 45 percent / imidazole / CH₂Cl₂ / 16 h / 21 °C

6: 99 percent / diisobutylaluminum hydride / toluene / 1.5 h / -78 °C

7: bromine, triphenylphosphine, triethylamine / CH₂Cl₂ / 1 h / -78 °C

With 1H-imidazole; copper(l) iodide; hydrogen fluoride; bromine; titanium tetrachloride; diisobutylaluminium hydride; triethylamine; triphenylphosphine; In diethyl ether; dichloromethane; toluene; acetonitrile;
DOI:10.1139/v95-278

Reference yield:

: 150665-29-5
4-(tert-butyldimethylsilyloxy)methyl-3,3-dimethyl-2-formyl(dimethylacetal)cyclohexanone

: 174788-43-3
2-bromomethyl-1,3,3-trimethyl-4-(tert-butyldimethylsilyloxy)methylcyclohex-1-ene

Guidance literature:: Multi-step reaction with 5 steps

1: 95 percent / toluene; diethyl ether / 0.67 h / 0 - 21 °C

2: hydrogen fluoride / acetonitrile / 0.25 h / Heating

3: 45 percent / imidazole / CH₂Cl₂ / 16 h / 21 °C

4: 99 percent / diisobutylaluminum hydride / toluene / 1.5 h / -78 °C

5: bromine, triphenylphosphine, triethylamine / CH₂Cl₂ / 1 h / -78 °C

With 1H-imidazole; hydrogen fluoride; bromine; diisobutylaluminium hydride; triethylamine; triphenylphosphine; In diethyl ether; dichloromethane; toluene; acetonitrile;
DOI:10.1139/v95-278